How to fail at almost everything and still win big

How to fail at almost everything and still win big

“I find it helpful to see the world as a slot machine that doesn’t ask you to put money in. All it asks is your time, focus, and energy to pull the handle over and over.” – Scott Adams

Most autobiographical self-help books on success recommend a “work hard”, “stay focused”, “never give up” doggedness. This book is one of the few that makes a direct reference to the role of luck in living a successful life. The typical tone of self-help books “I have it all figured out so let me tell you” is refreshingly missing in this one as Scott borrows from his own experiences with the repeated disclaimer that this is what worked for him and to rely on science and a smart friend to decide what you should apply directly. Needless to say, it has the irreverence, especially for conventional wisdom, authority and experts, albeit toned down, that made Dilbert a classic.

Core themes of the book

I grouped the takeaways from the book into seven core themes. In the process, I’ve omitted several anecdotes from Scott’s life that feed into these themes and also some of the specifics on how he recommends eating better and making exercise a regular part of your life. If you’ve struggled with those, might well be worth buying the book to get a non-expert but practitioner’s perspective on making progress.

The Core themes from ‘How to fail at almost everything and still win big’.

Passion is Bullshit – Most literature on success mistakenly identifies passion as the secret ingredient

Lessons from his failures from trying his hand at several ventures, many of them dating back to his 16 years as a corporate employee

To be successful, adopt a Systems over Goals mindset

The only thing that matters is managing your personal energy, often conflated with passion

Managing your attitude to remain optimistic leads to favourable outcomes, often by chance

A set of generic skills that improve anyone’s odds of success

Understanding that we are “moist robots” that can be programmed to be happier and how

The next three mindmaps drill down one level into the seven themes.

Scott summarises 22 different projects that ended in failure including two computer games that he coded himself, one website that asked people to submit “crackpot ideas”, an online video-streaming site that came before youtube, a substantial initial investment in webvan (of dot-com crash fame), a food product – the Dilberito, and two restaurants. He calls out timing (luck) as one of the critical elements of success (like with the video-streaming idea) and stays consistent towards the end by crediting it as one of the causes of Dilbert’s blockbuster success.

The “aha” material in the book is about choosing Systems over Goals. According to his definition, Goals are end-objectives coming from sizable effort, typically not achievable in a day while Systems are smaller steps, that when repeated move you along the path to something bigger.

A goal-oriented person is perpetually dissatisfied right up until the fleeting moment when they achieve their goal (become Vice President by 30 / Lose 10 kgs / Beat the market). This means more time spent feeling inadequate and therefore chances of giving up from discouragement. A systems-oriented person replaces the goal with the process that will get her to the goal as the focus. It might seem like a semantic difference but imagine the continuous positive feedback of setting your fitness target to “workout five days a week” over “lose 10 kgs and sport a six-pack” and it starts to make sense.

The 2nd most powerful takeaway from the book is the concept of managing your personal energy by observing yourself to note when you’re at your best and your worst and scheduling tasks accordingly. If you’re at your problem-solving best in the morning, don’t waste that advantage by checking and responding to mindless administrative emails. Leave the emails to coincide with your late afternoon slump. Cal Newport’s book – Deep Work makes a similar point about consciously carving out time.

“A person with a flexible schedule and average resources will be happier than a rich person who has everything except a flexible schedule”

Anyone who has been in a high-paying 70-80 hour/week job can relate to that statement.

Continuing from managing personal energy, Scott suggests our moods can also be managed if we realise the drivers; exercise, sleep and food. A message that he reiterates as tools to become a happier person. If you’re unhappy (in a bad mood), chances are you’re deficient in at least one of five things: a flexible schedule, imagination, sleep, diet and exercise.

In closing out the book, Scott again refers to luck:

People who seem to have good luck are often the people who have a system that allows luck to find them

The overlap with another book I recently read and mind-mapped, Max Gunther’s How to get Lucky is just coincidental. Probably.